When to Go
We spent four nights here in mid-July, during the off-season, and it was quiet in the best way—no crowds, no waiting, no need to book or reserve activities in advance. The weather was hot (it is Jamaica in July, after all), but the ocean breeze was a great way to cool down. There’s A/C in the rooms, but much of the resort is designed around open-air living, which could lead to some admittedly toasty cocktail hours and meals. All that to be said, we had no issue enjoying our mornings and evenings despite the heat, and, during the day, it was easy to cool off with a dip in the pool, wading in the ocean, or sitting under the shade of a tropical tree.
Round Hill is intentionally small and I've been told never feels crowded, even in peak season. Friends who have visited during winter and early spring have shared they still never had to fight for a beach chair or navigating large groups, and absoloutely savored their mornings and evenings al fresco. If you can swing the price increase associated with a visit in January or February, as well as taking time off outside of summertime, I think that would be the most ideal time of year to find yourself at Round Hill.
Getting There
Flights from the East Coast are easy—we flew nonstop from Atlanta to MBJ in under three hours.
Round Hill is just a quick 25-minute drive from the Montego Bay airport, and we booked private transportation directly through the hotel, which made everything seamless. For tipping throughout the trip, we used U.S. dollars, which are widely accepted, but I recommend pulling out plenty of small bills in advance to make it easy for gratuities for your transportation and at the hotel.
We also highly recommend adding Club Mobay to your itinerary—it gave us fast-track service through customs on arrival, and expedited security with access to a comfortable lounge on the way home (with drinks, snacks, and Wi-Fi while you wait for your flight). It’s well worth it, especially during busier travel times.
Where to Stay
We booked an Oceanfront Room in the 36-room Pineapple House, designed by Ralph Lauren (who also owns a villa on property—the only one not available to rent!). Think whitewashed walls, shuttered windows, dark wood finishes, and uninterrupted ocean views. The shuttered doors open wide, making indoor/outdoor living completely seamless—I spent slow mornings sipping coffee on the private patio and lazy late afternoons after showering reading on the room’s cozy built-in daybed. There are no TVs in the Pineapple House rooms, which I genuinely appreciated—it made it that much easier to unwind, unplug, and be present. It was perfect for two people looking to slow down and stay put.
If you’re traveling with a group or family, the private villas are truly something special. Round Hill has 27 villas, each one individually owned and uniquely designed, ranging from two to six bedrooms. Many come with private pools, expansive verandas, lush tropical gardens, and incredible ocean views. Each villa includes a dedicated staff, including a housekeeper, cook, and landscapers.
Several of the villas have ties to notable names and longtime guests—the Kennedy family members, Paul McCartney, and Grace Kelly over the decades. Timeless and secluded, these villas are a perfect setup for a multi-generational trip, girls’ getaway, or an extraordinarily luxurious and romantic celebration.
Dining
The food here is a standout—award-winning, thoughtful, and deeply rooted in Jamaican flavors. Round Hill has received accolades for its cuisine, and it shows in everything from the fresh juices at breakfast to the beautifully plated dinners under the stars. You can choose between a dining plan (which includes breakfast, lunch, and dinner for a fixed price daily) or go à la carte, depending on how much flexibility you want. We passed on the dining plan since our travel advisor, Grey, secured us free breakfast with our reservation!
Breakfasts were a continental spread with fresh fruit, bacon, sausage, pastries (including gluten free toast!), a variety of egg based dishes, and other morning time sweet meals like pancakes or waffles. I obsessed over the strong Blue Mountain coffee and freshly blended smoothies.
Lunch could be enjoyed in a few different settings—the elegant white-tablecloth terrace, poolside under striped umbrellas, or casually at the beach bar with your toes in the sand. The menu offered a thoughtful mix of classic seaside favorites like lobster rolls and jerk chicken nachos, alongside lighter bites such as grilled chicken spring rolls.
One of our favorite touches was the beachfront cart, where you could sip fresh coconuts, cut open right in front of you (and spiked with a splash of rum if you were feeling frisky!) and try house-made ice cream featuring Jamaican fruits like soursop and mango. Throughout the day, the staff would occasionally pass around surprise afternoon treats, like frozen bananas dipped in chocolate—a nostalgic and perfect pick-me-up between swims.
Of course, a favorite touch of mine was the Afternoon Tea held every afternoon at 4pm. This was yet another classic callback to holidays of yore, and the selection of beverages and bites was exquisite (gluten free cookies were available, too!).
Dinners were relaxed and candlelit, with rotating menus featuring classic Jamaican cuisine, along with other fine dining specialties. There’s a touch of formality in the evenings—after 7:30pm, men are required to wear pants in the dining room, which adds to the resort’s classic, refined feel. One standout was the Monday night beach barbecue, a Round Hill tradition for over 70 years, complete with live music. It was festive, casual, and clearly a beloved highlight for both new and returning guests.
For those slow, stay-in nights, there’s also a full room service menu available throughout the day, making it easy to enjoy a private dinner on your patio or breakfast in bed with an ocean view.
Activites
At Round Hill, there’s as much—or as little—to do as you’d like. Whether you’re craving quiet rest or a day full of activities, the resort makes it easy to follow your own pace.
We started each morning with coffee and fresh fruit on the balcony, followed by a leisurely breakfast on the oceanfront terrace. From there, we rotated between lounging at the pool and the beach, with short walks, swims, and rounds of travel mahjong on the terrace in between.
In the afternoons, we’d read, nap, and order drinks from the beach bar, where the view alone feels like a luxury. We also made time to shop the local artisan market set up on the property—filled with handwoven baskets, art, and ceramics that made for meaningful keepsakes and gifts.
One day, we booked a romantic couples massage at the secluded spa, tucked into the jungle hillside. You could hear the waves crashing and birds calling as you completely melted into the experience—truly one of the most peaceful hours of the trip, with a finale of champagne as we watched the sunset off a rocky pier.
While we relished in doing absolutely nothing, if you are a vacationer that needs a little activity, the resort is known for its tennis and pickleball offerings, and the resort also offers excursions, water sports, and plenty of off-the-beach snorkeling for the more adventurous.
Evenings were often spent unwinding on the lobby lanai with a game of cards, or tucked away enjoying a libation in the Ralph Lauren designed cocktail bar, with all the elegance of an old school New York City haunt, but overlooking paradise, peppered with photographs from the resort's star-studded history.
Our absolute favorite experience, however, was the historic villa tour, led by Junior, a longtime staff member with over 40 years at Round Hill. He shared the resort’s rich history while guiding us through some of the most historic and architecturally stunning villas—including those where John F. Kennedy drafted his inaugural address and Oscar Hammerstein wrote The Sound of Music. It was an unforgettable glimpse into the old-world glamour and legacy of the resort, along with some of the most magnificent architecture, design, and views that I think this world has to offer.
Final Thoughts
We absolutely would return to Round Hill—it’s one of those places that lingers with you long after you’ve left. It’s so easy to get to from the East Coast, making it perfect for a mini-moon, anniversary trip, or just a luxurious long weekend.
We stayed four nights, which was lovely, but I think five would have been the sweet spot—long enough to fully settle in, unwind, and still leave on a high note (I was actively begging Carter to tack on another night while our departure car was pulling up . . . so do with that what you will). We also noticed plenty of families with young children, and heard wonderful things about the on-site childcare and nanny program, which makes sense—everything about the resort feels intentionally designed to be both relaxing and easy, no matter your stage of life.
What surprised me at first, but makes absolute sense upon leaving, was how many guests we met who had been returning to Round Hill for decades. It’s a vacation spot that feels more akin to a country club—private, elevated, elegant, but lived in. It’s the kind of place where you’re just as comfortable in a linen cover-up as you are in eveningwear, where the staff knows your name by the second day, and where time somehow slows down in the best way.
